


Within Reach

by allyz



Category: Actor RPF, British Actor RPF, Hollanders - Fandom, Marvel, Marvel Cinematic Universe, Spider-Man (Tom Holland Movies), tom holland - Fandom, tom holland Fandom
Genre: Angst with a Happy Ending, CEO Tom Holland, Eventual Happy Ending, Eventual Romance, F/M, Fluff and Angst
Language: English
Status: In-Progress
Published: 2020-10-15
Updated: 2020-10-15
Packaged: 2021-03-08 19:48:28
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,075
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27022264
Author URL: https://archiveofourown.org/users/allyz/pseuds/allyz
Summary: You work as Tom's secretary, You're basically his shadow for almost a decade. With that being said, you two had known everything about each other. Well, except for one thing. You're quitting.
Relationships: Harrison Osterfield & You, Harrison Osterfield/Reader, Tom Holland (Actor) & Reader, Tom Holland (Actor)/Reader, Tom Holland (Actor)/You, Tom Holland/Harrison Osterfield
Kudos: 13





	1. Heads up Boss, I'm quitting.

**Author's Note:**

> Reposting this series and updating it with the new chapters! Hope you like it!

You have been working as Tom Holland’s secretary for almost a decade. You have witnessed everything he’s done for the past eight years. You’ve been beside him for too long that you could no longer recall a time when you weren’t under Tom’s beck and call.

Mr. Holland as a boss wasn’t a piece of cake. Apart from having to deal with all his busy schedule as the successor of one of the biggest companies in the country, you also had to deal with a great pain in the ass. Sure, he’s adored by many. Followed around by gorgeous women and paparazzi. It seemed like he had everything within his reach. Except for one thing. You.

Ever since you started working for him he was nothing but a complete jerk to you. Arguing about the smallest things. Tom bickering on how you lack the experience to even become a suitable secretary. Nonetheless, he has kept you in leash for years. The thought of why he even bothered to hire you comes to your mind at times. But you knew if you brought it up, he’d just shrug and tell you to just do your job better. Yes, you attempted to quit multiple times, but he always manages to come up with new set of benefits and multiple raises just so you wouldn’t leave. Of course, you’re just a person paying her dues. Back then, you had so many things on your plate. You had to help and look after your sister. You had to pay off loans and the debt your parents left you from when they died. You shouldered all the load and became your sister’s guardian at the same time. With that, how can you leave a job that’s been paying you tons of money just to make you stay? For you, it was just a way of setting priorities straight.

Over the years of working together, despite Mr. Holland still being a hardheaded dirtbag, you managed to work with him efficiently. You’ve figured out the ins and outs of the great Tom Holland. Before, your heart would go wild, and your palms would be sweaty just by the beep of the answering machine. But now, you even manage to outwit him by your snarky comebacks and the fact that he could ‘slightly’ no longer boss you around. Of course, you let him every now and then since that’s practically your job.

The machine beeped. That signals you to come in his office. You pick up his next week’s schedule. You saw him almost buried down with how many pile of files he has on his desk. He’s busy reading weekly reports. You’re not even surprised that despite all this, he’s still able to come to work in a perfectly neat suit and hair perfectly slick you could literally smell the pomade he uses.

You greeted him and handed him the folder. “Here’s your schedule for next week.” You were about to place it on his desk when he grabs it from you. He reviews it intently. As if he’s carefully finding the one thing you missed. Even if there was none.

He nodded as a response. “Don’t forget that you’ll have to face some of your business partners in order to secure their alliance.” You reminded. Mr. Holland goes on dinner/s, you obviously arranged, with partners coming in from various companies.

This was just a way for him to be in touch with his lady friends.

“Who am i meeting tonight?” he asked. His brows still frowned from reading reports after another. You can tell by the looks of it that he’s had a really long day. You should’ve noticed it by the number of teacups you’ve sent earlier. 

You smiled and answered. “No one. You have the night to yourself.” Assuming that he’s still the same Holland you knew that’s always full of himself, you already know what he’s about to do next.

He stopped and looked at you. “How come?” He said whilst leaning back and crossing his arms on his chest. Acting all disappointed that he’d be forced to go home alone. You stifled a grin from when what you thought was right.

“No one made appointments today, sir.” He fixes his position and leaned his elbows on the table. With intertwined fingers under his chin, he said, “You make an appointment.”

You failed to hide the puzzled look on your face. Before you even had the chance to speak, he talked again. “Perhaps, you and i catch up instead. After all, we both consider each other more than just boss and employee, am i right?”

A mischievous grin was plastered across his face. You think for a few seconds. Trying so hard to avert his eyes. “No offense, but may i ask why?” Great. That went out a little off. He manages to maintain his gaze on you. Memorizing every corner of your face. Noticing hints of freckles he has never seen before. You return his gaze frustrated from not being able to discern what’s running through his mind. 

“Ms. Y/N?” You snapped out of it the moment you heard his voice. Despite all the confusion you’re trying to suppress, you managed to put on a small smile. “Okay. Sure. Is there anything else I can help you with?” 

He shook his head. You turned your back so quickly completely missing the chance to see him smirking behind your face.

What the hell was that? You thought for a second. You absentmindedly walk back to your desk. You’ve gone to a lot of lunch and dinner meetings with him but this time it felt different. “Why doesn’t it feel normal? I’ve done this numerous times.” You shrugged off the thoughts running around your mind. You’re just overreacting. Don’t succumb to the way he asked you out. No no, he didn’t ask you out—don’t even start thinking it. But what did he mean by ‘we’re more than just boss and employee’? A thought came across you. 

As Tom’s secretary, it’s in the job description to be with him almost every day. You always have to ensure he gets all that he needs. And when he doesn’t you put even more effort and basically go out your way just to give it to him. From filing up reports, pushing deadlines, to giving him tea and snacks in between office hours. Tom isn’t the type of guy who likes to be ‘spoon-fed’ with these type of things. But because you’re the one doing it, he doesn’t mind. In fact, when he’s in a really good mood, he notices the littlest things you do for him. He just wouldn’t tell you. Why would he?

Half an hour passed since the two of you talked. You’re just finishing up a few details for the meeting tomorrow. The door to his office swung open. You quickly stood and the sight of the bachelor was all you can see. With him having both his hands in his pocket, it’s undeniable that women won’t fall with such stance. He walks toward you slightly scratching his temple. “You ready?”

You simply nodded. Before you even pick up your stuff he’s already walking towards the lift. Boy, was he always in a rush? You quickly caught up to him and matched his pace. 

You arrived at the restaurant. It was one of his favorites. Tom was already a regular at this place. That’s why he’s given a little more treatment than usual. You, on the other hand, being the one who books his every endeavor, you’re also greeted smiles by the staff. Tom walks to his table, not having the slightest courtesy to even wait for you. You sat in front of him as your server gives both of your usual. This was one of the things you can list on why it’s also good to work for the guy. 

“So..” He starts carving through his steak as you hand him his napkin, completely unfolded. You were about to cut yours when he lifts the plate up and switched it with his. Now, you had his steak. “Eat up.” Despite knowing he rarely shows chivalry, you thank him for cutting the meat himself. 

You go through the night with the usual stuff you talk about, work. It was evident that tom was quite a workaholic. You remember your first day of working for him. He told you two things he hates about a person. One who doesn’t start work on time, and one that doesn’t leave work on time. This was the only thing you held on for the first few years of working for him. You were really careful about going to work before he even arrives and leaving work on the dot. As the both of you totally immersed in the moment, you completely forgot the very thing that pushed you out of bed in the morning. 

Inattentively, you cut off whatever Tom was saying. Entirely forgetting the fact that he doesn’t want people cutting off his sentences. “I almost forgot; I have something to give you.” For a moment, you see Tom’s face lit up. He was about to break a smile when you handed him a white envelope complete with all your personal details. 

“What’s this?” With a confused look, he opens the envelope. 

“It’s my resignation letter.” 

The expression that was once printed all over his face was now entirely gone. In a heartbeat, Tom recalled all that has happened the week before this dreadful moment. It frustrates him that he cannot even come up with a viable reason for your wanting to leave. 

Each second without hearing Tom respond was making you anxious. He doesn’t say a word for another before opening the letter. What he saw wasn’t an immediate one but still, knowing now that you wanted to quit made him utterly frustrated. 

He asks you why. Like he always did. You clasped your hands together on your lap before answering. You’ve been thinking of finally quitting and leaving his side for good. Not because of how hard work has been for you, and to be honest, even though it was, you actually enjoyed every minute of it. It’s just that now you were finally done with the things you wanted to accomplish ever since you started working. You finally bought yourself your own flat. You’ve already sent your sister to a good university. Where she’s doing pretty well. Really, all of your immediate plans were already accomplished. Now that your plate’s free from all the weight it once carried, you can’t help but dream of a life that’s meant to be lived by you. And only you. Neither a life spent taking care of others nor taking care of Tom.

“Nothing. Just personal reasons.” You kept the details all to yourself because for some reason, you’re afraid it’d be funny once you said it out loud. You won’t let that happen. Especially not while you’re facing Tom.

Knowing how he usually reacts, you prepare yourself for all the reasons he’s going to give you just to stop you from leaving. Tom on the other hand, is still having a hard time digesting the recent information. Sure, he can live without you by his side, he knows that all too well. He just chooses not to.

“I won’t accept this for merely personal reasons. I’m sure you don’t take me for a fool, ’m i right?” he casually said taking a sip of wine. You watch him arch his back, making himself comfortable. You know he does this when he’s being confident.

“I won’t let you off my hook just to see you after your new boss’ shadow.” He added. Tom was always good at showing he’s dominant and far ahead from you. Normally, you’ll let this slide and even feed his ego. But it’s different. You want this. And you’re gonna get it.

You placed the wine glass down, “I’m sorry but I am not asking for your permission.” You smiled before continuing, “I’m just giving you a heads up.”

“I won’t be leaving work right away, especially without having anyone to attend to your needs. But I promise you to provide an even better secretary after me.”

You’re surprised Tom wasn’t butting in so you continue. He’s looking at you all stunned by the sight of the new side of you. One he didn’t expect. Yes, you’re persistent but when it comes to him, he knew that he doesn’t even have to repeat himself. You just quickly submit after his demands. Perhaps, he thought he still had a hold of you.

You now have your hands on the table. Determined to make him say yes. Determined to finally make him let you go. “I will train her and make her suitable in the office within a month.”

“And I promise that I won’t fail and disappoint you.” Tom saw the eagerness in your eyes. His heart getting heavier. He was nothing but clueless that he doesn’t know how to react. He straightens up and loosened his tie.

You fight the urge to fix it. Since that was what you always did for him. Looking at his tie all crooked now was like a tick you can’t wait to get rid of. You managed not to and kept your hands to yourself. Instead, you put your focus on what he’s about to say.

He said nothing. He just stood up—didn’t even bother to thank you for having dinner with him and started walking away. You were left dumbfounded as you watch his back. Once he was out of your sight, with a hint of you wanting him to look back, you sighed, slumping on the chair, finishing a glass of wine in seconds.


	2. For fuck's sake, a namesake?

**Summary for the Chapter:**

> You were not the only one keeping secrets from your boss. Who's Y/N anyway?

You wake up to the sunlight streaming on your face. You ran your hands through your sheets and felt comfort. Nothing feels better than having a good night’s sleep. You got up and went straight to the kitchen to brew yourself some tea. Leaning towards the counter you thought about the events that took place last night. There’s no way Tom would’ve forgotten about the talk you had. You just wish he’d be a little more understanding once you meet him at work. Last night was clearly not the way you wanted to deliver such news. But that’s completely off the table now. You tell yourself that it’s better that way. At least you’ve already told him and it’s already out in the open.

You got off the shower realizing that you haven’t checked the time. You picked up your phone which was buzzing non-stop. It’s now 8 in the morning. You only have an hour left to finish and arrive to work on time. You checked the continuous messages you’ve been getting.

You frowned upon seeing Amber’s endless texts. What’s up with her? She rarely messages you this early.

“Ms. Y/N, where are you?”

“Mr. Holland came in early!!!”

“And girls kept showing up with resumes and stuff.”

“Do you know anything about this?”

“I already told the guys and they’re all clueless as me!”

“Please come now, it’s quite urgent!”

A couple more messages were buried underneath but you didn’t let another second put to waste. You rushed off and did all your routine as fast as you could. You were still in shock that he showed up at work before you. What was with all the girls showing up at the office?

You almost stumble upon every step you took towards the lift. Regardless, this wasn’t new to you. Tom always did things that made you sprint from one place to another.

“What’re you up to this time?” You mumble to yourself as you wait for the doors to open.

You walk past the front desk completely ignoring a few greetings on your way. You felt bad but you figured they’ll understand since seeing you like this isn’t really a surprise.

“Ms. Y/N!” You saw Amber running towards you, eager to meet you halfway. Neither of you stopped to greet each other as both of you are now walking towards the same direction. Amber tries her best to catch up to you and gave you the details you needed.

“Fifteen people have already gone to his office. All of them were sent away.” She nervously told you.

“Where is he?” Your gaze completely fixated on the path. People are literally moving out of your way as you and Amber walk past them.

“He’s still inside. Should I- Should I knock-” You cut her off since that was a dumb idea.

“Are you nuts?”

“Come on.” You slowed down as you arrive at your desk. You quietly slid in and sat to your seat whilst peeking towards his office.

“Are you gonna get fired?” Amber whispered behind you. Tom gave you a pretty large space in front of his office and that gave her a chance to hide and peep with you. You looked at her and hushed. Preventing any more side comments coming from her.

By the time you returned to what you were doing, your eyes widened when you met his gaze back. His dark brown eyes stared back at you. Almost as cold as ice. A gaze that was quickly broken when Tom shut the blinds. The last thing you saw was him grinning at the sight of whoever was in front of him.

“Why! What happened!” Amber exclaimed from underneath. Right. She was still there.

“He’s grinning—well, almost laughing. Did you saw the last person going inside?” She shook her head.

Even though you wouldn’t let yourself admit it, seeing Tom chuckle that way set you off. Especially when he doesn’t even do that. Amber tapped your arm lightly. Awkwardly smiling and gesturing that she’s going back to her desk. You nodded and dismissed her.

You tried your best to distract yourself by updating records on the screen. What’s taking so long? You thought. You keep glancing back just to see the same blinds that pushed you away earlier. After a good 10-minute torture went by, the machine beeped. Making you jump in anticipation. You made sure you were well-composed before entering the room.

The sight you saw when you entered was two people formally talking to each other. A girl possibly in her mid-20s sat across Tom. With hair barely touching her shoulder, and curls complementing the shape of her face, you take it that she was just a young lass like you once were when you first worked for the man.

You saw Tom acknowledged your presence. You smiled before making your way in between them. With clasped hands, you waited in silence.

Tom broke the ice and said, “Ms. Y/N, please meet Y/N.”

With the both of you still processing the unusual introduction, your namesake stood and handed out her hand.

“It’s a pleasure to meet you, I’m Y/NS Gray.”

It was a while before you finally took her hand and shook it. “I’m Y/N Y/L/N.”

“She’ll be the one replacing you.” Tom stood, quite liking the scene in front of him.

“W-Wait, really? I’m hired?” Y/NS gushed in disbelief. She put a hand on her chest trying to conceal her dramatic breathing. Inadvertently, you rolled your eyes. Fucking fake drama.

“Well yes, only if you want it.” Tom lightly scratches his right brow. Throwing off soft chuckles that seemed to make your namesake’s heart flutter.

You stared at Tom who’s now clueless on what to do next. His hands flailing all over the place unable to decide where he should rest them. Finally, he puts them in his pocket and looked at you.

“I guess Ms. Y/N would be taking it from here.” You scoffed. You guess???

You fake a cough to mask your rudeness. “Shall we?”

Gesturing the novice towards the door, she looked back at Tom once last time and bid her goodbye. You stormed off the place as you hear the clack of her heels follow you.

Y/NS closed the door behind and stood beside you. You, on the other hand, unsure of what to do next, being that you never had anyone else take over your position, you just had to address the elephant in the room. Or at least the only thing that was bothering you at the moment.

“How should I address you?” You turned and looked at her. Your hair sliding off your shoulders.

“Uhm.” Y/NS looked at you with confusion plastered all over her face.

“Oh.” She replied, slowly catching up on what you meant.

“Oh. About that. I guess i should go by Anna. That’s my second name.”

“Alright, Anna.” You let out a pleasing look and showed her to the desk. You cleared up some space for her and let her settle in. Meanwhile, you caught a few heads out and about. Intently eavesdropping. Desperate to catch more and more information.

You pretended not to see. You’ll deal with them in a minute.

“Here are the basics you should know. It’s all in there so that’d be a great help.” You hand her a folder you once spent nights studying. It contained all the things you needed to learn about Tom and the company.

You hesitated to let go of your grip as she tried to take the folder from you. It was the only thing that made you different from all the other employees. And you hated the fact that somebody’s going to be that person as well. Soon after you leave, she’s going to be you. And she’ll only be thanking you for that.

Anna was busy going through the stuff you gave her. You walk towards the pantry as eyes followed you all the way.

It wasn’t long until people came scrambling towards the door. All with sheepish smiles. You put a hand on your waist and arched an eyebrow. You can’t help but laugh at the scene made by your colleagues.

“What was that all about?”

“Are you getting replaced?”

“No, Wait–are you fired??”

“Why was she hired right away?”

“Is she from Harvard?”

“Hey— why do you always think it’s gonna be someone from Harvard??”

“Look, guys, stop.” You raised a hand signaling them to break the talk off. You let go of a sigh before answering them.

“First of all, I’m leaving.” Once you let that one go, more questions were thrown at you as if it was the only thing circling around the workplace.

“Bu-Bu-But!!!!” Cutting them off whilst pointing a finger up to make the ringing stop.

“BUT—I won’t be leaving right away. Once I’ve groomed her and she becomes fit for the job, that’s the time I’m gonna have to. Tom and I already talked about it and with him conducting interviews already–I think it’s finally going to happen.”

They all looked at you with saddened eyes. With pressed lips, you can’t help but admit that you’re really gonna miss these people.

Amber slowly races her hand and speaks, “We heard you both share the same name. We don’t need any more Y/Ns. You’re the only Ms. Y/N we’re ever going to have.” You felt the sincerity in her voice. These people gave you the title. You didn’t think you deserved to be treated as a superior but here you were, admired by the very faces you eat lunch with on most days.

“Ugh, I hate you.” You wiped your eyes to prevent yourself from tearing up. The last thing you don’t want to do is to cry in front of them. You opened your arms widely and gestured for a hug. They all came crashing into you. Saying all wonderful things that only made your heart swell.

Remember, these are the people you’re going to leave.

The moment got interrupted when the blonde Y/NS entered the room. Silence enveloped the place. Alienating the new girl. You nudged Amber forcing her to crack a smile. The rest followed the both of you and expressed their polite hospitality.

“Hey.” Anna waved. “I was told to bring Mr. Holland his tea.”

“Oh, don’t worry. I’ll take care of it.” You smiled at her as you began doing the errand.

Anna seemed to have read the room and quickly caught on. She nodded and went on her way back.

“I don’t even think that’s her real hair color,” Amber whispered to your side. You gave her a side-eye and let go of a small laugh as you watch them leave you to your business.

Carrying with you a tea tray, you managed to knock on the door before letting yourself in. Tom was too preoccupied to notice you were even in the room. He was standing meters away from you busy flipping pages after pages.

You walked towards his table.

“Ms. Y/N.” He called. Slightly racing his voice to make sure you hear him across the room.

“Yes?” You gladly answered as you put down the tray.

Tom looks up and was taken aback when he saw you.

“Why are you here?” He said.

You bit your lower lip by his recent note. Bemused, you said, “I came by to give you your tea?”

Just like you always did.

You looked at him still unsure of why he had to ask. His eyes trailed to the tray you put down a while ago.

“I asked Y/N to do that. She should be the one doing that from now on.” His frigid voice sent chills down your spine. He looked at you with eyes empty of emotion. And when it took you a while to answer, he briskly turned away and returned to his task.

You slowly carried on your way leaving the room all to himself.

You spent half the day fazed by how Tom treated you earlier. You managed to make Anna do all the extra work and now she’s just sitting beside you massaging her ankles. It probably got sore from all the walking she had to do. You also told her that Tom wanted her to bring his tea instead. She reluctantly obliged at first because by what she told you, it looked like you wanted to do it yourself. You dismissed the notion so you’d just been watching her send Tom teas and snacks all morning.

The huge door that has been dominating the workplace for years swung open. You and Anna were already on your feet when Tom came out.

“Ms. Y/N.” Instinctively, both of you answered. Uncertain of who Tom was referring to this time.

“I meant, Ms. Gray.” His frame turning over to her side. You on the other hand quietly sat yourself down and pretended to carry on what you were doing.

“Please be at the meeting later to record the minutes.”

“You can have lunch.” He added, sort of throwing the words into thin air, unsure of who’s it for, before heading out on his way.

You let out a sigh. Troubled by how difficult it was for you to take everything in.

Meanwhile, Tom went to the other side of the floor and barged in another room.

“Don’t you ever learn how to knock?” A man, the same with his age, looked at Tom annoyed and caught off guard.

Just like Tom’s, his desk was occupied by folders neatly spread out below him. He was a man with hair that has streaks of gold in it. The hair that you secretly adored. The hair that makes Tom want to rip it all out every time he catches you staring at it.

With a loosened tie, almost showing his clavicles off, his eyeglasses slid down his nose; clearly, this was a man who needs to distress. Even though you saw him in this state countless times, you’re sure that this was a view girls in the workplace would die for.

Next to a bottle of whiskey was a nameplate that read, Harrison Osterfield Vice President.

Tom stopped for a moment. “Please don’t tell me what you’re doing before I came in here.”

The man rolled his eyes catching up on what Tom meant. He gave him an ‘Oh, please.’ look as he stood and sat across Tom who was proud enough to let himself comfortable on the couch.

“What are you doing here?” He scratches the back of his head. Utterly annoyed with Tom’s sudden appearance.

Tom was never bothered by Harrison’s bluntness towards him. In fact, this was one of the things he’s glad about him. Harrison never gave a fuck about Tom being an heir to his father. Hell, he didn’t even care that Tom was now practically his boss. For him, Tom was just Tom. The Thomas he knew ever since he was a kid. The brother he had for years.

With legs crossed and both his hands on his nape, he said, “Why? You don’t want me here?”

“Uh, duh?” Tom ignored his remark and showed off a grin.

“I heard you made a scene earlier, huh? What’s with all the ladies, mate?” Harrison teased.

“I uh, actually hired a new secretary,” Tom announced as he fixes his position. Beginning to sound serious.

Harrison furrowed his brows with confusion. “Is this about last night?”

Tom just nodded.

“She’s done this numerous times. How could you be so bothered?” It’s true. You did have a fair share of resignation letters sent over to Mr. Holland’s desk.

To be frank, If there was a third person involved to all Tom’s affairs, it will be you. Because Harrison was the second. Almost all things related to you, he knows because of Tom.

Yes, Tom is equally close to his brothers but the bond you saw between him and Haz was different. They’d bicker and fight most days. But in the end, they’ll always come back laughing it off. You just know they’ll always have each other’s backs. Out of all the friendships Tom has had in the past eight years, this one’s your favorite. 

Tom shook his head. “I don’t know man, it seemed like it might be for good this time. And I don’t think I can do anything about it.”

“Sure you do—and you know it.” He picks up a glass of whiskey before resting his back.

“Just stop fuckin’ around, Tom.”

**Author's Note:**

> Always a sucker for what you have to say! Let me know what you think ♡


End file.
